(2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

• ChemBase ID: 132966
• Molecular Formular: C26H52NO7P
• Molecular Mass: 521.667341
• Monoisotopic Mass: 521.34813964
• SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O
• Canonical SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OCC[N+](C)(C)C)[O-])O
• InChI: InChI=1S/C26H52NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h12-13,25,28H,5-11,14-24H2,1-4H3/b13-12-/t25-/m1/s1
• InChIKey: YAMUFBLWGFFICM-PTGWMXDISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
• IUPAC Traditional name: (2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
• Synonyms: (7R,18Z)-4,7-Dihydroxy-N,N,N-trimethyl-10-oxo-,3,5,9-trioxa-4-phosphaheptacos-18-en-1-aminium Inner Salt 4-Oxide; 1-O-Oleoyl-sn-glycero-3-phosphocholine; 1-Oleoyl-sn-glycero-3-phosphocholine; 1-Oleoyl-sn-glycero-3-phosphocholine; (7R,18Z)-4,7-Dihydroxy-N,N,N-trimethyl-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18-en-1-aminium 4-oxide, inner salt; 1-(9Z-Octadecenoyl)-sn-glycero-3-phosphocholine; 1-cis-9-Octadecenoyl-sn-glycero-3-phosphocholine; 1-Oleoyl-2-hydroxy-sn-glycerol-3-phosphocholine; 1-Oleoyl-sn-glycero-3-phosphorylcholine; 3-sn-Lysophosphatidylcholine, 1-oleoyl; L-γ-Oleoyl-α-lysolecithin; Lysolecithin, oleoyl; PC(18:1(9Z)/0:0); PC(18:1/0:0); 1-Oleoyl-sn-glycero-3-phosphocholine

Database IDs

• CAS Number: 19420-56-5
• MDL Number: MFCD00133435
• Beilstein Number: 4033747
• PubChem SID: 162227243; 24896294
• PubChem CID: 16081932

CALCULATED PROPERTIES

• Acid pKa: 1.8553406
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.7434618
• LogD (pH = 7.4): 3.743558
• Log P: 1.7199582
• Molar Refractivity: 152.5923 cm^3
• Polarizability: 56.246002 Å^3
• Polar Surface Area: 105.12 Å^2
• Rotatable Bonds: 25
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ~99%
• Biological Source: synthetic

DETAILS

Toronto Research Chemicals - O528040

1-Oleoyl-sn-glycero-3-phosphocholine is a marker contained in biological sample for determination of obesity and screening method.

REFERENCES

• Hanke, C., et al.: Eur. J. Biochem., 232, 806 (1995)
• Bao, X., et al.: Plant Physiol., 118, 183 (1995)
• Benghezal, M., et al.: J. Biol. Chem., 282, 30845 (1995)
• Cao, J., et al.: J. Biol. Chem., 283, 19049 (1995)